Angelology can be used to explain human evil in different ways. This chapter compares Milton's ideas to those of an early eighteenth-century Jewish mystic. Milton brings the scholastic tradition to a point of literary clarity, thus exposing a weakness at its foundation. For interpreting human evil by reference to an anthropomorphically depicted angelic sphere drives explanation into regress, exposing an homunculus fallacy. The pivotal anthropomorphic element is angelic freewill, which is central to Milton's work. I compare this perspective to a kabbalistic conception by which angelic rebelliousness is explained as false cognitive states within the angel, produced by its incomprehension of the purpose of its own divine mission to challenge humans to sin. I explain how this is a form of cognitive dissonance, and that angels are here employed as a median sphere to explain human weakness in a structural manner and to interpret evil as founded upon such dissonance.